Herbicidal Compounds

Abstract

The present invention relates to herbicidally active thiazolopyridinones, in particular benzyloxy-substituted-phenyl-thiazolopyridinone derivatives, of formula (I), wherein R 1 , R 2 , G, X, Y, Z and n are as defined herein. The invention further provided processes for their preparation, and compositions comprising such derivatives. The invention also extends to the use of such compounds and compositions as herbicides, i.e. for the control of undesirable plant growth. In particular such compounds and compositions may be used in controlling weeds, such as broad-leaved dicotyledonous weeds, in crops of useful plants.

1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         or a salt or N-oxide thereof, 
         wherein: 
         R 1  is hydrogen, halogen, nitro, cyano, or selected from the group consisting of : C 1 -C 6 alkyl, C 2 -C 6  alkenyl, C 1 -C 6  alkoxy C 1 -C 6  alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 cycoalkyl, C 1 -C 6  alkoxy-C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy-, di-C 1 -C 6 alkoxy-C 1 -C 6 alkyl, and C 1 -C 6 alkylthio-C 1 -C 6 alkyl, each of which is optionally substituted by 1-3 halogen atoms; 
         R 2  is hydrogen; or C 1 -C 6 alkyl, C 2 -C 6  alkenyl, C 3 -C 6 alkynyl C 3 -C 6 cycoalkyl, C 1 -C 6  alkoxy-C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy-, di-C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 alkyl, C 1 -C 6 alkylsulfinyl-C 1 -C 6 alkyl, C 1 -C 6 alkylsulfonyl-C 1 -C 6 alkyl, C 3 -C 6 cycoalkyl-C 1 -C 6 alkyl, or cyano-C 1 -C 6 alkyl, each of which is optionally substituted by 1-3 halogen atoms; or phenyl optionally substituted by 1-3 substituents independently selected from halogen, C 1 -C 6  alkyl and C 1 -C 6  alkoxy; or benzyl optionally substituted by 1-3 substituents independently selected from halogen, C 1 -C 6  alkyl and C 1 -C 6  alkoxy; 
         G is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl or aryl-C 1 -C 4 alkyl- or aryl-C 1 -C 4 alkyl- wherein the aryl moiety is substituted by one to five substituents independently selected from halo, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy, or C(O)R 3′ ; 
         R 3  is C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkyl-C 1 -C 10 alkyl-, C 1 -C 10 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 4 alkoxy-C 1 -C 10 alkyl-, C 1 -C 4 alkylthio-C 1 -C 4 alkyl-, C 1 -C 10 alkoxy, C 2 -C 10 alkenyloxy, C 2 -C 10 alkynyloxy, C 1 -C 10 alkylthio-, NR 5 R 6 , N—C 1 -C 4 alkyl-amino-, N,N-di-(C 1 -C 4 alkyl)-amino-, aryl or aryl substituted by 1-3 R 4 , which may be the same or different, heteroaryl or heteroaryl substituted by 1-3 R 4 , which may be the same or different, aryl-C 1 -C 4 alkyl- or aryl-C 1 -C 4 alkyl- wherein the aryl moiety is substituted by 1-3 to three R 4 , which may be the same or different, heteroaryl-C 1 -C 4 alkyl- or heteroaryl-C 1 -C 4 alkyl- wherein the heteroaryl moiety is substituted by 1-3 R 4 , which may be the same or different, aryloxy- or aryloxy-substituted by 1-3 R 4 , which may be the same or different, heteroaryloxy- or heteroaryloxy-substituted by 1-3 R 4 , which may be the same or different, arylthio- or arylthio-substituted by 1-3 R 4 , which may be the same or different, or heteroarylthio- or heteroarylthio-substituted by one to three R 4 , which may be the same or different; 
         each R 4  is independently halo, cyano, nitro, C 1 -C 10 alkyl, C 1 -C 4 haloalkyl, C 1 -C 10 alkoxy, C 1 -C 4 alkoxycarbonyl-, C 1 -C 4 haloalkoxy, C 1 -C 10 alkylthio-, C 1 -C 4 haloalkylthio-, C 1 -C 10 alkylsulfinyl-, C 1 -C 4 haloalkylsulfinyl-, C 1 -C 10 alkylsulfonyl-, C 1 -C 4 haloalkylsulfonyl-, aryl or aryl substituted by 1-5 substituents independently selected from halo, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 5 haloalkyl or C 1 -C 6 alkoxy, or heteroaryl or heteroaryl substituted by 1-4 substituents independently selected from halo, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy; 
         R 5  and R 6  are independently selected from the group consisting of C 1 -C 6  alkyl and C 1 -C 6  alkoxy, or R 5  and R 6  together can form a morpolinyl ring; 
         X and Y are each independently hydrogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen, 
         Z is C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen; and 
         n is an integer of 0, 1, 2, 3, 4, or 5. 
       
     
     
         2 . The compound according to  claim 1 , wherein R 1  is hydrogen, or selected from the group consisting of: C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy-, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl and C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, each of which is optionally substituted by 1-3 halogen atoms. 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . The compound according to  claim 1 , wherein R 1  is hydrogen. 
     
     
         6 . The compound according to  claim 1 , wherein R 2  is hydrogen or selected from the group consisting of: C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, and cyano-C 1 -C 6 -alkyl, each of which is optionally substituted by 1-3 halogen atoms; or optionally substituted phenyl or optionally substituted benzyl, wherein said optional substituents are 1-3 substituents independently selected from halogen, C 1 -C 6 alkyl, and C 1 -C 6 alkoxy. 
     
     
         7 . (canceled) 
     
     
         8 . (canceled) 
     
     
         9 . The compound according to  claim 1 , wherein R 1  is hydrogen and R 2  is methyl, difluoroethyl, trifluoroethyl, or propargyl. 
     
     
         10 . The compound according to  claim 1  wherein X is hydrogen, halogen, or C 1 -C 3 haloalkyl. 
     
     
         11 . (canceled) 
     
     
         12 . The compound according to  claim 1  wherein Y is hydrogen, C 1 -C 3  alkyl, C 1 -C 3 haloalkyl, or halogen. 
     
     
         13 . The compound according to  claim 1  wherein n is 0, 1, or 2. 
     
     
         14 . The compound according to  claim 1  wherein each Z is independently selected from halogen, methyl, methoxy, and trifluoromethoxy. 
     
     
         15 . The compound according to  claim 1  wherein G is C(O)R 3 , and R 3  is selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 1 -C 6 alkyl-S—, —NR 4 R 5  and phenyl optionally substituted by one or more R 7 . 
     
     
         16 . The compound according to  claim 1  wherein G is C(O)NR 4 R 5 , and R 4  and R 5  are independently selected from the group consisting of C 1 -C 6  alkyl and C 1 -C 6  alkoxy, or R 4  and R 5  together can form a morpolinyl ring. 
     
     
         17 . (canceled) 
     
     
         18 . The compound according to  claim 1 , wherein G is hydrogen. 
     
     
         19 . A herbicidal composition comprising a herbicidal compound according to  claim 1  and an agriculturally acceptable formulation adjuvant. 
     
     
         20 . A herbicidal composition according to  claim 19 , further comprising at least one additional pesticide. 
     
     
         21 . A herbicidal composition according to  claim 20 , wherein the additional pesticide is a herbicide or herbicide safener. 
     
     
         22 . A method of controlling unwanted plant growth, comprising applying a compound of formula (I) as defined in  claim 1  to the unwanted plants or to the locus thereof. 
     
     
         23 . (canceled) 
     
     
         24 . The compound of  claim 1 , wherein:
 R 1  is hydrogen;   R 2  is methyl, difluoroethyl, trifluoroethyl, or propargyl;   X is hydrogen, halogen, or C 1 -C 3 haloalkyl;   Y is hydrogen, C 1 -C 3  alkyl, C 1 -C 3 haloalkyl, or halogen;   Z is independently selected from halogen, methyl, methoxy, and trifluoromethoxy;   n is 0, 1, or 2; and   G is hydrogen.